# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 Cu N10 S2' _chemical_formula_weight 520.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M p_-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.469(3) _cell_length_b 10.956(3) _cell_length_c 12.770(4) _cell_angle_alpha 70.023(4) _cell_angle_beta 68.500(4) _cell_angle_gamma 87.844(4) _cell_volume 1152.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1538 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 25.70 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.301 _exptl_crystal_size_mid 0.241 _exptl_crystal_size_min 0.171 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 538 _exptl_absorpt_coefficient_mu 1.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.844 _exptl_absorpt_correction_T_max 0.908 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6125 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.70 _reflns_number_total 4295 _reflns_number_gt 3006 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4295 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.61471(5) 0.37435(5) 0.41339(4) 0.04100(19) Uani 1 1 d . . . C1 C 0.7198(5) 0.2347(5) 0.6130(4) 0.0543(11) Uani 1 1 d . . . C2 C 0.8474(5) 0.2379(4) 0.2355(4) 0.0449(10) Uani 1 1 d . . . C3 C 0.8394(5) 0.6391(4) 0.3183(4) 0.0470(10) Uani 1 1 d . . . C4 C 0.8583(5) 0.7609(4) 0.2285(4) 0.0539(12) Uani 1 1 d . . . H4A H 0.9326 0.8286 0.2042 0.065 Uiso 1 1 calc R . . C5 C 0.7494(5) 0.7630(4) 0.1828(4) 0.0478(10) Uani 1 1 d . . . C6 C 0.9288(5) 0.5875(5) 0.3949(4) 0.0592(12) Uani 1 1 d . . . H6A H 0.8717 0.5125 0.4627 0.089 Uiso 1 1 calc R . . H6B H 0.9494 0.6535 0.4225 0.089 Uiso 1 1 calc R . . H6C H 1.0234 0.5629 0.3491 0.089 Uiso 1 1 calc R . . C7 C 0.7164(5) 0.8691(4) 0.0868(4) 0.0588(12) Uani 1 1 d . . . H7A H 0.7820 0.9468 0.0618 0.088 Uiso 1 1 calc R . . H7B H 0.6119 0.8865 0.1177 0.088 Uiso 1 1 calc R . . H7C H 0.7340 0.8423 0.0193 0.088 Uiso 1 1 calc R . . C8 C 0.3606(5) 0.1232(4) 0.5484(4) 0.0441(10) Uani 1 1 d . . . C9 C 0.2340(5) 0.0892(4) 0.5282(4) 0.0517(11) Uani 1 1 d . . . H9A H 0.1709 0.0113 0.5705 0.062 Uiso 1 1 calc R . . C10 C 0.2204(5) 0.1900(4) 0.4363(4) 0.0471(10) Uani 1 1 d . . . C11 C 0.4226(5) 0.0434(4) 0.6388(4) 0.0538(11) Uani 1 1 d . . . H11A H 0.4855 0.0992 0.6515 0.081 Uiso 1 1 calc R . . H11B H 0.4826 -0.0194 0.6099 0.081 Uiso 1 1 calc R . . H11C H 0.3399 -0.0012 0.7132 0.081 Uiso 1 1 calc R . . C12 C 0.1060(5) 0.2028(5) 0.3793(4) 0.0692(15) Uani 1 1 d . . . H12A H 0.0567 0.2807 0.3811 0.104 Uiso 1 1 calc R . . H12B H 0.0313 0.1283 0.4227 0.104 Uiso 1 1 calc R . . H12C H 0.1564 0.2078 0.2974 0.104 Uiso 1 1 calc R . . C13 C 0.3781(4) 0.4068(4) 0.3170(3) 0.0388(9) Uani 1 1 d . . . C14 C 0.5430(4) 0.5874(4) 0.2379(3) 0.0391(9) Uani 1 1 d . . . C15 C 0.3584(5) 0.5823(4) 0.1692(3) 0.0452(10) Uani 1 1 d . . . C16 C 0.1634(5) 0.5673(5) 0.0904(4) 0.0569(12) Uani 1 1 d . . . H16A H 0.0961 0.6289 0.0645 0.068 Uiso 1 1 calc R . . H16B H 0.1047 0.5076 0.1708 0.068 Uiso 1 1 calc R . . C17 C 0.2184(6) 0.4914(5) 0.0072(4) 0.0750(15) Uani 1 1 d . . . H17A H 0.1325 0.4467 0.0080 0.113 Uiso 1 1 calc R . . H17B H 0.2834 0.4289 0.0333 0.113 Uiso 1 1 calc R . . H17C H 0.2745 0.5501 -0.0730 0.113 Uiso 1 1 calc R . . C18 C 0.3417(6) 0.7730(4) 0.0091(4) 0.0618(13) Uani 1 1 d . . . H18A H 0.3712 0.8240 0.0480 0.074 Uiso 1 1 calc R . . H18B H 0.2573 0.8114 -0.0118 0.074 Uiso 1 1 calc R . . C19 C 0.4752(6) 0.7821(5) -0.1058(5) 0.0834(17) Uani 1 1 d . . . H19A H 0.5032 0.8719 -0.1575 0.125 Uiso 1 1 calc R . . H19B H 0.4464 0.7337 -0.1461 0.125 Uiso 1 1 calc R . . H19C H 0.5604 0.7466 -0.0863 0.125 Uiso 1 1 calc R . . N1 N 0.5018(4) 0.4646(3) 0.3146(3) 0.0425(8) Uani 1 1 d . . . N2 N 0.4239(3) 0.2406(3) 0.4733(3) 0.0392(8) Uani 1 1 d . . . N3 N 0.7228(4) 0.5658(3) 0.3294(3) 0.0429(8) Uani 1 1 d . . . N4 N 0.6768(4) 0.3120(3) 0.5514(3) 0.0475(9) Uani 1 1 d . . . N5 N 0.7721(4) 0.2904(4) 0.2948(3) 0.0543(9) Uani 1 1 d . . . N6 N 0.3372(3) 0.2824(3) 0.4019(3) 0.0404(8) Uani 1 1 d . . . N7 N 0.6681(4) 0.6434(3) 0.2444(3) 0.0422(8) Uani 1 1 d . . . N8 N 0.3016(4) 0.4576(3) 0.2487(3) 0.0433(8) Uani 1 1 d . . . N9 N 0.4794(4) 0.6518(3) 0.1634(3) 0.0447(8) Uani 1 1 d . . . N10 N 0.2897(4) 0.6394(3) 0.0945(3) 0.0485(9) Uani 1 1 d . . . S1 S 0.77986(17) 0.12408(14) 0.70721(13) 0.0754(4) Uani 1 1 d . . . S2 S 0.95763(14) 0.16278(13) 0.14956(11) 0.0639(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0432(3) 0.0391(3) 0.0430(3) -0.0088(2) -0.0242(2) 0.0054(2) C1 0.048(3) 0.062(3) 0.057(3) -0.024(2) -0.020(2) -0.008(2) C2 0.042(2) 0.045(2) 0.046(2) -0.009(2) -0.022(2) -0.0010(19) C3 0.040(2) 0.049(3) 0.053(3) -0.021(2) -0.017(2) 0.004(2) C4 0.046(3) 0.043(2) 0.062(3) -0.011(2) -0.014(2) -0.004(2) C5 0.048(2) 0.037(2) 0.050(2) -0.0093(19) -0.014(2) 0.0009(19) C6 0.048(3) 0.065(3) 0.073(3) -0.024(3) -0.032(2) 0.004(2) C7 0.068(3) 0.041(2) 0.056(3) -0.002(2) -0.024(2) 0.002(2) C8 0.049(2) 0.039(2) 0.041(2) -0.0076(19) -0.020(2) 0.0045(19) C9 0.049(2) 0.046(3) 0.055(3) -0.003(2) -0.026(2) -0.012(2) C10 0.042(2) 0.050(3) 0.050(2) -0.011(2) -0.024(2) -0.001(2) C11 0.055(3) 0.040(2) 0.059(3) 0.001(2) -0.030(2) -0.002(2) C12 0.057(3) 0.072(3) 0.075(3) -0.002(3) -0.041(3) -0.012(3) C13 0.040(2) 0.041(2) 0.034(2) -0.0077(18) -0.0173(18) 0.0056(18) C14 0.043(2) 0.036(2) 0.039(2) -0.0119(18) -0.0184(18) 0.0074(18) C15 0.050(3) 0.045(2) 0.040(2) -0.0109(19) -0.021(2) 0.015(2) C16 0.054(3) 0.062(3) 0.056(3) -0.011(2) -0.033(2) 0.013(2) C17 0.098(4) 0.065(3) 0.067(3) -0.021(3) -0.038(3) 0.008(3) C18 0.080(3) 0.049(3) 0.066(3) -0.012(2) -0.048(3) 0.019(2) C19 0.099(4) 0.067(4) 0.063(3) 0.001(3) -0.029(3) 0.009(3) N1 0.0442(19) 0.0335(18) 0.050(2) -0.0071(15) -0.0251(16) 0.0030(15) N2 0.0411(18) 0.0395(19) 0.0404(18) -0.0098(15) -0.0236(15) 0.0086(15) N3 0.0438(19) 0.0383(18) 0.049(2) -0.0106(16) -0.0251(16) 0.0068(15) N4 0.052(2) 0.044(2) 0.044(2) -0.0013(16) -0.0269(18) 0.0005(17) N5 0.054(2) 0.054(2) 0.059(2) -0.022(2) -0.024(2) 0.0070(19) N6 0.0367(18) 0.0425(19) 0.0386(18) -0.0054(15) -0.0184(15) 0.0004(15) N7 0.0417(19) 0.0374(18) 0.0442(19) -0.0057(15) -0.0204(16) 0.0043(15) N8 0.0442(19) 0.045(2) 0.0416(19) -0.0079(16) -0.0240(16) 0.0047(16) N9 0.049(2) 0.0407(19) 0.044(2) -0.0088(16) -0.0238(17) 0.0094(16) N10 0.056(2) 0.048(2) 0.044(2) -0.0085(16) -0.0294(18) 0.0134(17) S1 0.0798(9) 0.0692(9) 0.0795(9) -0.0063(7) -0.0508(8) 0.0076(7) S2 0.0614(8) 0.0721(8) 0.0588(8) -0.0262(7) -0.0215(6) 0.0177(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 1.942(3) . ? Cu N4 1.956(3) . ? Cu N3 2.101(3) . ? Cu N2 2.102(3) . ? Cu N5 2.134(4) . ? C1 N4 1.120(5) . ? C1 S1 1.641(5) . ? C2 N5 1.133(5) . ? C2 S2 1.638(5) . ? C3 N3 1.326(5) . ? C3 C4 1.396(6) . ? C3 C6 1.479(6) . ? C4 C5 1.354(6) . ? C4 H4A 0.9300 . ? C5 N7 1.362(5) . ? C5 C7 1.494(5) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N2 1.314(5) . ? C8 C9 1.402(6) . ? C8 C11 1.487(5) . ? C9 C10 1.352(5) . ? C9 H9A 0.9300 . ? C10 N6 1.366(5) . ? C10 C12 1.489(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N8 1.302(4) . ? C13 N1 1.338(5) . ? C13 N6 1.381(5) . ? C14 N9 1.302(5) . ? C14 N1 1.334(5) . ? C14 N7 1.396(5) . ? C15 N10 1.319(5) . ? C15 N9 1.365(5) . ? C15 N8 1.377(5) . ? C16 N10 1.484(6) . ? C16 C17 1.503(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N10 1.465(5) . ? C18 C19 1.520(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N2 N6 1.397(4) . ? N3 N7 1.385(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N4 159.26(14) . . ? N1 Cu N3 76.30(13) . . ? N4 Cu N3 100.64(13) . . ? N1 Cu N2 76.75(13) . . ? N4 Cu N2 100.68(13) . . ? N3 Cu N2 150.93(12) . . ? N1 Cu N5 99.87(14) . . ? N4 Cu N5 100.86(14) . . ? N3 Cu N5 97.67(14) . . ? N2 Cu N5 97.48(13) . . ? N4 C1 S1 177.8(4) . . ? N5 C2 S2 179.5(4) . . ? N3 C3 C4 110.2(4) . . ? N3 C3 C6 120.3(4) . . ? C4 C3 C6 129.4(4) . . ? C5 C4 C3 108.0(4) . . ? C5 C4 H4A 126.0 . . ? C3 C4 H4A 126.0 . . ? C4 C5 N7 105.4(4) . . ? C4 C5 C7 130.2(4) . . ? N7 C5 C7 124.3(4) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C9 110.5(4) . . ? N2 C8 C11 121.8(4) . . ? C9 C8 C11 127.7(4) . . ? C10 C9 C8 107.7(4) . . ? C10 C9 H9A 126.1 . . ? C8 C9 H9A 126.1 . . ? C9 C10 N6 105.9(3) . . ? C9 C10 C12 129.2(4) . . ? N6 C10 C12 124.9(4) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N8 C13 N1 126.0(4) . . ? N8 C13 N6 121.7(4) . . ? N1 C13 N6 112.3(3) . . ? N9 C14 N1 126.5(4) . . ? N9 C14 N7 121.6(4) . . ? N1 C14 N7 111.9(3) . . ? N10 C15 N9 117.7(4) . . ? N10 C15 N8 117.7(4) . . ? N9 C15 N8 124.6(4) . . ? N10 C16 C17 112.9(4) . . ? N10 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? N10 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N10 C18 C19 113.8(4) . . ? N10 C18 H18A 108.8 . . ? C19 C18 H18A 108.8 . . ? N10 C18 H18B 108.8 . . ? C19 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C14 N1 C13 115.1(3) . . ? C14 N1 Cu 122.7(3) . . ? C13 N1 Cu 122.2(3) . . ? C8 N2 N6 105.1(3) . . ? C8 N2 Cu 142.9(3) . . ? N6 N2 Cu 111.6(2) . . ? C3 N3 N7 104.7(3) . . ? C3 N3 Cu 142.2(3) . . ? N7 N3 Cu 112.6(2) . . ? C1 N4 Cu 150.9(4) . . ? C2 N5 Cu 174.7(4) . . ? C10 N6 C13 132.5(3) . . ? C10 N6 N2 110.8(3) . . ? C13 N6 N2 116.6(3) . . ? C5 N7 N3 111.7(3) . . ? C5 N7 C14 132.4(3) . . ? N3 N7 C14 115.9(3) . . ? C13 N8 C15 113.9(3) . . ? C14 N9 C15 113.8(3) . . ? C15 N10 C18 120.8(4) . . ? C15 N10 C16 120.8(4) . . ? C18 N10 C16 118.4(3) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.70 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.473 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 921713' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 N10 Ni S2' _chemical_formula_weight 515.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M p_-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8512(18) _cell_length_b 11.923(2) _cell_length_c 13.480(3) _cell_angle_alpha 65.61(3) _cell_angle_beta 89.96(3) _cell_angle_gamma 70.44(3) _cell_volume 1205.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 1.006 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.742 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8151 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4055 _reflns_number_gt 2716 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0935P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4055 _refine_ls_number_parameters 293 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1675 _refine_ls_wR_factor_gt 0.1520 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.18613(7) 0.76343(5) 0.19077(5) 0.0453(2) Uani 1 1 d . . . C1 C 0.3422(6) 0.7474(5) 0.4090(5) 0.0506(12) Uani 1 1 d . . . C2 C -0.0716(5) 0.9308(5) -0.0551(4) 0.0445(11) Uani 1 1 d . . . C3 C 0.5357(6) 0.6923(5) 0.1032(4) 0.0548(13) Uani 1 1 d . . . C4 C 0.6440(6) 0.5762(6) 0.1004(5) 0.0678(16) Uani 1 1 d . . . H4A H 0.7420 0.5672 0.0735 0.081 Uiso 1 1 calc R . . C5 C 0.5817(6) 0.4806(5) 0.1433(4) 0.0569(13) Uani 1 1 d . . . C6 C 0.5471(7) 0.8233(6) 0.0675(5) 0.0758(18) Uani 1 1 d . . . H6A H 0.4942 0.8630 0.1136 0.114 Uiso 1 1 calc R . . H6B H 0.4951 0.8788 -0.0078 0.114 Uiso 1 1 calc R . . H6C H 0.6593 0.8137 0.0735 0.114 Uiso 1 1 calc R . . C7 C 0.6442(8) 0.3399(6) 0.1606(6) 0.082(2) Uani 1 1 d . . . H7A H 0.7435 0.3217 0.1311 0.123 Uiso 1 1 calc R . . H7B H 0.5651 0.3252 0.1238 0.123 Uiso 1 1 calc R . . H7C H 0.6641 0.2824 0.2382 0.123 Uiso 1 1 calc R . . C8 C -0.1566(6) 0.8319(5) 0.2845(5) 0.0649(16) Uani 1 1 d . . . C9 C -0.2488(7) 0.7574(5) 0.3420(5) 0.0711(18) Uani 1 1 d . . . H9A H -0.3456 0.7891 0.3659 0.085 Uiso 1 1 calc R . . C10 C -0.1725(6) 0.6317(5) 0.3565(5) 0.0582(14) Uani 1 1 d . . . C11 C -0.1901(8) 0.9769(6) 0.2452(7) 0.099(3) Uani 1 1 d . . . H11A H -0.0894 0.9900 0.2490 0.148 Uiso 1 1 calc R . . H11B H -0.2570 1.0086 0.2913 0.148 Uiso 1 1 calc R . . H11C H -0.2454 1.0248 0.1704 0.148 Uiso 1 1 calc R . . C12 C -0.2161(7) 0.5126(5) 0.4117(5) 0.0753(18) Uani 1 1 d . . . H12A H -0.3091 0.5333 0.4467 0.113 Uiso 1 1 calc R . . H12B H -0.1263 0.4420 0.4662 0.113 Uiso 1 1 calc R . . H12C H -0.2410 0.4855 0.3578 0.113 Uiso 1 1 calc R . . C13 C 0.0930(6) 0.5332(4) 0.2964(4) 0.0447(11) Uani 1 1 d . . . C14 C 0.3247(5) 0.4865(4) 0.2275(4) 0.0438(11) Uani 1 1 d . . . C15 C 0.2223(7) 0.3299(5) 0.3090(5) 0.0595(15) Uani 1 1 d . . . C16 C 0.1210(16) 0.1448(12) 0.4461(13) 0.189(6) Uani 1 1 d U . . H16A H 0.1704 0.0504 0.4988 0.227 Uiso 1 1 d R . . H16B H 0.0775 0.1972 0.4880 0.227 Uiso 1 1 d R . . C17 C 0.0311(19) 0.1723(12) 0.3624(10) 0.200(8) Uani 1 1 d . . . H17A H -0.0616 0.1487 0.3834 0.300 Uiso 1 1 calc R . . H17B H 0.0896 0.1240 0.3236 0.300 Uiso 1 1 calc R . . H17C H -0.0044 0.2656 0.3153 0.300 Uiso 1 1 calc R . . C18 C 0.3788(8) 0.1064(5) 0.3315(5) 0.0770(18) Uani 1 1 d . . . H18A H 0.4735 0.1301 0.3317 0.092 Uiso 1 1 calc R . . H18B H 0.4021 0.0199 0.3926 0.092 Uiso 1 1 calc R . . C19 C 0.3472(9) 0.1001(8) 0.2279(7) 0.111(3) Uani 1 1 d . . . H19A H 0.4408 0.0365 0.2198 0.167 Uiso 1 1 calc R . . H19B H 0.3246 0.1856 0.1673 0.167 Uiso 1 1 calc R . . H19C H 0.2554 0.0743 0.2284 0.167 Uiso 1 1 calc R . . N1 N 0.2088(5) 0.5747(4) 0.2502(3) 0.0454(10) Uani 1 1 d . . . N2 N -0.0288(5) 0.7581(4) 0.2624(3) 0.0506(10) Uani 1 1 d . . . N3 N 0.4094(5) 0.6697(4) 0.1472(3) 0.0485(10) Uani 1 1 d . . . N4 N 0.2958(5) 0.7513(4) 0.3280(4) 0.0591(12) Uani 1 1 d . . . N5 N -0.1387(5) 1.0440(4) -0.1048(4) 0.0528(11) Uani 1 1 d . . . N6 N -0.0342(5) 0.6331(4) 0.3067(3) 0.0478(10) Uani 1 1 d . . . N7 N 0.4365(4) 0.5382(4) 0.1727(3) 0.0457(10) Uani 1 1 d . . . N8 N 0.3375(5) 0.3663(4) 0.2510(3) 0.0512(10) Uani 1 1 d . . . N9 N 0.0914(5) 0.4141(4) 0.3289(4) 0.0576(12) Uani 1 1 d . . . N10 N 0.2376(7) 0.2052(4) 0.3467(5) 0.0820(17) Uani 1 1 d . . . S1 S 0.02418(17) 0.77120(12) 0.01477(12) 0.0593(4) Uani 1 1 d . . . S2 S 0.4135(2) 0.74232(16) 0.52333(13) 0.0709(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0473(4) 0.0327(3) 0.0495(4) -0.0116(3) 0.0086(3) -0.0151(3) C1 0.048(3) 0.043(3) 0.057(4) -0.016(3) 0.011(3) -0.020(2) C2 0.046(3) 0.041(3) 0.046(3) -0.016(2) 0.009(2) -0.021(2) C3 0.049(3) 0.063(3) 0.050(3) -0.017(3) 0.011(2) -0.028(3) C4 0.049(3) 0.077(4) 0.066(4) -0.025(3) 0.018(3) -0.018(3) C5 0.051(3) 0.057(3) 0.050(3) -0.017(3) 0.014(2) -0.013(3) C6 0.073(4) 0.076(4) 0.082(5) -0.026(3) 0.026(3) -0.043(3) C7 0.081(4) 0.060(4) 0.087(5) -0.032(3) 0.030(4) -0.005(3) C8 0.054(3) 0.049(3) 0.090(5) -0.030(3) 0.032(3) -0.019(3) C9 0.053(3) 0.059(3) 0.104(5) -0.036(3) 0.035(3) -0.023(3) C10 0.056(3) 0.057(3) 0.067(4) -0.025(3) 0.024(3) -0.028(3) C11 0.091(5) 0.044(3) 0.155(7) -0.041(4) 0.063(5) -0.022(3) C12 0.080(4) 0.064(4) 0.090(5) -0.029(3) 0.044(4) -0.042(3) C13 0.052(3) 0.035(2) 0.043(3) -0.012(2) 0.009(2) -0.018(2) C14 0.046(3) 0.039(2) 0.039(3) -0.010(2) 0.005(2) -0.014(2) C15 0.076(4) 0.039(3) 0.063(4) -0.023(3) 0.022(3) -0.020(3) C16 0.188(10) 0.084(7) 0.290(16) -0.092(9) -0.052(10) -0.029(7) C17 0.307(19) 0.117(9) 0.185(13) -0.071(10) 0.170(14) -0.082(12) C18 0.103(5) 0.046(3) 0.079(5) -0.030(3) 0.016(4) -0.021(3) C19 0.106(6) 0.113(6) 0.128(7) -0.081(6) 0.009(5) -0.019(5) N1 0.047(2) 0.037(2) 0.046(2) -0.0124(18) 0.0115(19) -0.0155(18) N2 0.053(2) 0.036(2) 0.063(3) -0.020(2) 0.018(2) -0.0205(19) N3 0.047(2) 0.038(2) 0.052(3) -0.0113(19) 0.0051(19) -0.0172(18) N4 0.064(3) 0.052(3) 0.057(3) -0.019(2) 0.006(2) -0.023(2) N5 0.054(2) 0.037(2) 0.060(3) -0.015(2) -0.003(2) -0.0169(19) N6 0.048(2) 0.035(2) 0.058(3) -0.0182(19) 0.017(2) -0.0150(18) N7 0.043(2) 0.041(2) 0.047(3) -0.0144(18) 0.0085(19) -0.0143(18) N8 0.063(3) 0.036(2) 0.052(3) -0.0174(19) 0.015(2) -0.018(2) N9 0.071(3) 0.044(2) 0.065(3) -0.022(2) 0.024(2) -0.031(2) N10 0.110(4) 0.047(3) 0.106(4) -0.037(3) 0.055(3) -0.044(3) S1 0.0670(9) 0.0351(7) 0.0618(9) -0.0143(6) 0.0018(7) -0.0112(6) S2 0.0902(11) 0.0789(10) 0.0531(10) -0.0285(8) 0.0135(8) -0.0429(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni N5 1.987(4) 2_575 ? Ni N1 1.989(4) . ? Ni N4 2.018(5) . ? Ni N3 2.136(4) . ? Ni N2 2.141(4) . ? Ni S1 2.7252(18) . ? C1 N4 1.145(6) . ? C1 S2 1.636(6) . ? C2 N5 1.158(6) . ? C2 S1 1.633(5) . ? C3 N3 1.320(6) . ? C3 C4 1.411(7) . ? C3 C6 1.472(7) . ? C4 C5 1.346(7) . ? C4 H4A 0.9300 . ? C5 N7 1.384(6) . ? C5 C7 1.493(7) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N2 1.300(6) . ? C8 C9 1.404(7) . ? C8 C11 1.504(7) . ? C9 C10 1.349(7) . ? C9 H9A 0.9300 . ? C10 N6 1.398(6) . ? C10 C12 1.488(7) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N9 1.306(6) . ? C13 N1 1.329(6) . ? C13 N6 1.394(6) . ? C14 N8 1.298(6) . ? C14 N1 1.340(6) . ? C14 N7 1.391(6) . ? C15 N10 1.314(6) . ? C15 N8 1.362(6) . ? C15 N9 1.366(6) . ? C16 C17 1.238(17) . ? C16 N10 1.754(17) . ? C16 H16A 0.9865 . ? C16 H16B 0.9943 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.461(9) . ? C18 N10 1.485(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N2 N6 1.376(5) . ? N3 N7 1.392(5) . ? N5 Ni 1.987(4) 2_575 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Ni N1 168.53(17) 2_575 . ? N5 Ni N4 94.23(17) 2_575 . ? N1 Ni N4 97.21(17) . . ? N5 Ni N3 104.49(16) 2_575 . ? N1 Ni N3 75.63(15) . . ? N4 Ni N3 93.74(17) . . ? N5 Ni N2 103.21(16) 2_575 . ? N1 Ni N2 75.80(14) . . ? N4 Ni N2 91.18(17) . . ? N3 Ni N2 151.40(14) . . ? N5 Ni S1 88.33(13) 2_575 . ? N1 Ni S1 80.20(13) . . ? N4 Ni S1 175.85(12) . . ? N3 Ni S1 88.77(12) . . ? N2 Ni S1 85.06(12) . . ? N4 C1 S2 178.2(5) . . ? N5 C2 S1 179.6(5) . . ? N3 C3 C4 109.6(5) . . ? N3 C3 C6 120.1(5) . . ? C4 C3 C6 130.3(5) . . ? C5 C4 C3 108.6(4) . . ? C5 C4 H4A 125.7 . . ? C3 C4 H4A 125.7 . . ? C4 C5 N7 105.4(4) . . ? C4 C5 C7 131.5(5) . . ? N7 C5 C7 123.1(5) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C9 110.5(4) . . ? N2 C8 C11 120.0(4) . . ? C9 C8 C11 129.4(5) . . ? C10 C9 C8 108.1(4) . . ? C10 C9 H9A 125.9 . . ? C8 C9 H9A 125.9 . . ? C9 C10 N6 104.6(4) . . ? C9 C10 C12 130.8(5) . . ? N6 C10 C12 124.6(4) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N9 C13 N1 126.2(4) . . ? N9 C13 N6 121.4(4) . . ? N1 C13 N6 112.4(4) . . ? N8 C14 N1 126.6(4) . . ? N8 C14 N7 121.4(4) . . ? N1 C14 N7 112.0(4) . . ? N10 C15 N8 117.3(4) . . ? N10 C15 N9 118.1(5) . . ? N8 C15 N9 124.6(4) . . ? C17 C16 N10 81.2(12) . . ? C17 C16 H16A 116.8 . . ? N10 C16 H16A 116.1 . . ? C17 C16 H16B 116.5 . . ? N10 C16 H16B 115.8 . . ? H16A C16 H16B 108.6 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 N10 111.3(6) . . ? C19 C18 H18A 109.4 . . ? N10 C18 H18A 109.4 . . ? C19 C18 H18B 109.4 . . ? N10 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C13 N1 C14 114.5(4) . . ? C13 N1 Ni 122.1(3) . . ? C14 N1 Ni 122.2(3) . . ? C8 N2 N6 106.1(4) . . ? C8 N2 Ni 141.8(3) . . ? N6 N2 Ni 111.9(3) . . ? C3 N3 N7 105.8(4) . . ? C3 N3 Ni 142.1(4) . . ? N7 N3 Ni 112.1(3) . . ? C1 N4 Ni 172.8(4) . . ? C2 N5 Ni 162.8(4) . 2_575 ? N2 N6 C13 117.6(4) . . ? N2 N6 C10 110.6(4) . . ? C13 N6 C10 131.8(4) . . ? C5 N7 C14 131.9(4) . . ? C5 N7 N3 110.6(4) . . ? C14 N7 N3 117.3(4) . . ? C14 N8 C15 113.6(4) . . ? C13 N9 C15 113.9(4) . . ? C15 N10 C18 121.5(5) . . ? C15 N10 C16 119.0(5) . . ? C18 N10 C16 117.5(5) . . ? C2 S1 Ni 100.20(19) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.578 _refine_diff_density_min -0.639 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 921714' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 Co N10 S2' _chemical_formula_weight 515.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M p_-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7012(17) _cell_length_b 11.514(3) _cell_length_c 14.198(3) _cell_angle_alpha 85.868(4) _cell_angle_beta 75.758(4) _cell_angle_gamma 86.508(4) _cell_volume 1215.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1798 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 25.14 _exptl_crystal_description deepred _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 534 _exptl_absorpt_coefficient_mu 0.905 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.737 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6049 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4222 _reflns_number_gt 3095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4222 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1591 _refine_ls_wR_factor_gt 0.1493 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co Co 0.74063(7) 0.48082(5) 0.23663(4) 0.0452(2) Uani 1 1 d . . . C1 C 0.9567(6) 0.3058(4) 0.0912(3) 0.0510(10) Uani 1 1 d . . . C2 C 0.5255(5) 0.3455(4) 0.4215(3) 0.0493(10) Uani 1 1 d . . . C3 C 0.4000(6) 0.5124(4) 0.1311(3) 0.0513(11) Uani 1 1 d . . . C4 C 0.3072(6) 0.6096(5) 0.0968(3) 0.0618(13) Uani 1 1 d . . . H4A H 0.2114 0.6067 0.0681 0.074 Uiso 1 1 calc R . . C5 C 0.3819(6) 0.7080(4) 0.1130(3) 0.0551(11) Uani 1 1 d . . . C6 C 0.3720(7) 0.3874(4) 0.1300(4) 0.0684(14) Uani 1 1 d . . . H6A H 0.4654 0.3429 0.1521 0.103 Uiso 1 1 calc R . . H6B H 0.3745 0.3685 0.0649 0.103 Uiso 1 1 calc R . . H6C H 0.2578 0.3692 0.1723 0.103 Uiso 1 1 calc R . . C7 C 0.3452(7) 0.8311(5) 0.0859(4) 0.0734(14) Uani 1 1 d . . . H7A H 0.2428 0.8376 0.0583 0.110 Uiso 1 1 calc R . . H7B H 0.4475 0.8605 0.0390 0.110 Uiso 1 1 calc R . . H7C H 0.3213 0.8755 0.1428 0.110 Uiso 1 1 calc R . . C8 C 1.0641(6) 0.4639(4) 0.3544(3) 0.0486(10) Uani 1 1 d . . . C9 C 1.1624(6) 0.5471(4) 0.3867(3) 0.0524(11) Uani 1 1 d . . . H9A H 1.2482 0.5313 0.4224 0.063 Uiso 1 1 calc R . . C10 C 1.1076(5) 0.6529(4) 0.3556(3) 0.0445(9) Uani 1 1 d . . . C11 C 1.0676(7) 0.3352(4) 0.3716(4) 0.0622(12) Uani 1 1 d . . . H11A H 1.0562 0.3001 0.3142 0.093 Uiso 1 1 calc R . . H11B H 0.9699 0.3137 0.4252 0.093 Uiso 1 1 calc R . . H11C H 1.1790 0.3087 0.3864 0.093 Uiso 1 1 calc R . . C12 C 1.1646(6) 0.7714(4) 0.3708(4) 0.0602(12) Uani 1 1 d . . . H12A H 1.2569 0.7630 0.4058 0.090 Uiso 1 1 calc R . . H12B H 1.0635 0.8152 0.4074 0.090 Uiso 1 1 calc R . . H12C H 1.2098 0.8117 0.3087 0.090 Uiso 1 1 calc R . . C13 C 0.8671(5) 0.7102(3) 0.2660(3) 0.0374(8) Uani 1 1 d . . . C14 C 0.6372(5) 0.7272(3) 0.1944(3) 0.0401(9) Uani 1 1 d . . . C15 C 0.7469(5) 0.8862(3) 0.2351(3) 0.0461(10) Uani 1 1 d . . . C16 C 0.8656(8) 1.0543(4) 0.2866(5) 0.0792(16) Uani 1 1 d . . . H16A H 0.8752 1.1357 0.2638 0.095 Uiso 1 1 calc R . . H16B H 0.9836 1.0162 0.2664 0.095 Uiso 1 1 calc R . . C17 C 0.8065(9) 1.0463(5) 0.3966(5) 0.0960(19) Uani 1 1 d . . . H17A H 0.8912 1.0832 0.4228 0.144 Uiso 1 1 calc R . . H17B H 0.8003 0.9658 0.4197 0.144 Uiso 1 1 calc R . . H17C H 0.6904 1.0847 0.4171 0.144 Uiso 1 1 calc R . . C18 C 0.6060(8) 1.0748(4) 0.2046(5) 0.0827(17) Uani 1 1 d . . . H18A H 0.5896 1.0443 0.1456 0.099 Uiso 1 1 calc R . . H18B H 0.6492 1.1529 0.1884 0.099 Uiso 1 1 calc R . . C19 C 0.4282(8) 1.0805(5) 0.2785(6) 0.104(2) Uani 1 1 d . . . H19A H 0.3442 1.1296 0.2523 0.156 Uiso 1 1 calc R . . H19B H 0.4435 1.1119 0.3367 0.156 Uiso 1 1 calc R . . H19C H 0.3837 1.0036 0.2937 0.156 Uiso 1 1 calc R . . S1 S 1.06965(19) 0.20502(14) 0.02499(11) 0.0821(5) Uani 1 1 d . . . S2 S 0.41835(19) 0.28245(15) 0.52176(10) 0.0819(5) Uani 1 1 d . . . N4 N 0.8763(5) 0.3751(3) 0.1395(3) 0.0605(10) Uani 1 1 d . . . N5 N 0.6010(5) 0.3886(3) 0.3477(3) 0.0624(10) Uani 1 1 d . . . N3 N 0.5290(4) 0.5477(3) 0.1677(2) 0.0470(8) Uani 1 1 d . . . N1 N 0.7527(4) 0.6551(3) 0.2289(2) 0.0393(7) Uani 1 1 d . . . N2 N 0.9541(4) 0.5168(3) 0.3064(2) 0.0421(8) Uani 1 1 d . . . N6 N 0.9806(4) 0.6339(3) 0.3063(2) 0.0381(7) Uani 1 1 d . . . N7 N 0.5185(4) 0.6679(3) 0.1573(2) 0.0455(8) Uani 1 1 d . . . N8 N 0.6244(4) 0.8398(3) 0.1967(2) 0.0453(8) Uani 1 1 d . . . N9 N 0.8760(4) 0.8224(3) 0.2699(2) 0.0423(8) Uani 1 1 d . . . N10 N 0.7415(5) 1.0004(3) 0.2408(3) 0.0578(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.0464(4) 0.0388(3) 0.0481(4) -0.0060(2) -0.0059(2) -0.0027(2) C1 0.048(2) 0.069(3) 0.041(2) -0.013(2) -0.0150(19) -0.008(2) C2 0.043(2) 0.052(3) 0.056(3) -0.003(2) -0.017(2) 0.0029(19) C3 0.040(2) 0.075(3) 0.039(2) -0.008(2) -0.0050(18) -0.016(2) C4 0.047(3) 0.092(4) 0.050(3) -0.010(2) -0.017(2) -0.011(2) C5 0.047(2) 0.080(3) 0.038(2) -0.004(2) -0.0124(19) 0.006(2) C6 0.065(3) 0.080(4) 0.060(3) -0.014(2) -0.007(2) -0.026(3) C7 0.076(3) 0.083(4) 0.068(3) 0.012(3) -0.036(3) 0.003(3) C8 0.051(2) 0.049(2) 0.044(2) -0.0057(18) -0.0087(19) 0.0101(19) C9 0.050(3) 0.054(3) 0.056(3) -0.007(2) -0.021(2) 0.010(2) C10 0.038(2) 0.054(3) 0.043(2) -0.0067(18) -0.0124(18) -0.0008(18) C11 0.073(3) 0.050(3) 0.063(3) -0.004(2) -0.019(2) 0.010(2) C12 0.061(3) 0.061(3) 0.067(3) -0.006(2) -0.029(2) -0.010(2) C13 0.037(2) 0.036(2) 0.037(2) -0.0005(15) -0.0058(16) -0.0050(15) C14 0.038(2) 0.046(2) 0.036(2) -0.0022(16) -0.0074(16) -0.0032(17) C15 0.049(2) 0.043(2) 0.042(2) 0.0036(17) -0.0047(19) -0.0011(18) C16 0.097(4) 0.037(3) 0.111(5) 0.005(3) -0.040(4) -0.013(3) C17 0.130(6) 0.071(4) 0.096(5) -0.023(3) -0.044(4) 0.008(4) C18 0.089(4) 0.037(3) 0.128(5) 0.010(3) -0.041(4) -0.001(2) C19 0.082(4) 0.068(4) 0.167(7) -0.035(4) -0.034(4) 0.015(3) S1 0.0705(9) 0.0951(11) 0.0799(10) -0.0452(8) -0.0086(7) 0.0107(7) S2 0.0675(9) 0.1174(13) 0.0528(7) 0.0186(7) -0.0067(6) -0.0015(8) N4 0.058(2) 0.063(2) 0.063(2) -0.022(2) -0.0147(19) 0.0027(18) N5 0.054(2) 0.062(3) 0.068(3) 0.003(2) -0.010(2) -0.0065(18) N3 0.044(2) 0.050(2) 0.048(2) -0.0070(15) -0.0096(16) -0.0067(15) N1 0.0417(18) 0.0394(17) 0.0384(17) -0.0031(13) -0.0136(14) 0.0013(14) N2 0.0461(19) 0.0368(18) 0.0420(18) -0.0035(13) -0.0091(15) 0.0037(14) N6 0.0360(17) 0.0379(18) 0.0415(17) -0.0054(13) -0.0106(14) -0.0022(13) N7 0.0403(19) 0.051(2) 0.0449(19) -0.0052(15) -0.0108(15) 0.0026(15) N8 0.0465(19) 0.043(2) 0.0467(19) -0.0012(14) -0.0130(15) 0.0008(15) N9 0.0455(19) 0.0391(19) 0.0428(18) -0.0014(14) -0.0129(15) 0.0002(14) N10 0.067(3) 0.035(2) 0.073(3) 0.0025(17) -0.023(2) -0.0012(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co N5 1.958(4) . ? Co N4 1.963(4) . ? Co N1 2.008(3) . ? Co N3 2.175(4) . ? Co N2 2.191(3) . ? C1 N4 1.140(5) . ? C1 S1 1.619(5) . ? C2 N5 1.159(5) . ? C2 S2 1.606(5) . ? C3 N3 1.325(5) . ? C3 C4 1.412(7) . ? C3 C6 1.470(6) . ? C4 C5 1.361(7) . ? C4 H4A 0.9300 . ? C5 N7 1.393(5) . ? C5 C7 1.470(7) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N2 1.310(5) . ? C8 C9 1.421(6) . ? C8 C11 1.484(6) . ? C9 C10 1.345(6) . ? C9 H9A 0.9300 . ? C10 N6 1.371(5) . ? C10 C12 1.504(6) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N9 1.304(5) . ? C13 N1 1.342(5) . ? C13 N6 1.394(5) . ? C14 N8 1.296(5) . ? C14 N1 1.337(5) . ? C14 N7 1.394(5) . ? C15 N10 1.321(5) . ? C15 N8 1.353(5) . ? C15 N9 1.368(5) . ? C16 N10 1.468(6) . ? C16 C17 1.514(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N10 1.476(6) . ? C18 C19 1.508(8) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N3 N7 1.381(5) . ? N2 N6 1.376(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Co N4 109.08(17) . . ? N5 Co N1 124.71(15) . . ? N4 Co N1 126.10(15) . . ? N5 Co N3 100.34(14) . . ? N4 Co N3 100.93(14) . . ? N1 Co N3 74.31(12) . . ? N5 Co N2 95.79(15) . . ? N4 Co N2 99.10(14) . . ? N1 Co N2 74.21(12) . . ? N3 Co N2 148.46(12) . . ? N4 C1 S1 178.6(5) . . ? N5 C2 S2 178.0(4) . . ? N3 C3 C4 110.1(4) . . ? N3 C3 C6 120.4(4) . . ? C4 C3 C6 129.6(4) . . ? C5 C4 C3 108.3(4) . . ? C5 C4 H4A 125.8 . . ? C3 C4 H4A 125.8 . . ? C4 C5 N7 104.5(4) . . ? C4 C5 C7 130.8(5) . . ? N7 C5 C7 124.6(4) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C9 110.1(4) . . ? N2 C8 C11 120.5(4) . . ? C9 C8 C11 129.3(4) . . ? C10 C9 C8 107.0(4) . . ? C10 C9 H9A 126.5 . . ? C8 C9 H9A 126.5 . . ? C9 C10 N6 106.1(4) . . ? C9 C10 C12 129.5(4) . . ? N6 C10 C12 124.4(4) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N9 C13 N1 127.0(3) . . ? N9 C13 N6 119.9(3) . . ? N1 C13 N6 113.0(3) . . ? N8 C14 N1 126.6(3) . . ? N8 C14 N7 120.8(3) . . ? N1 C14 N7 112.5(3) . . ? N10 C15 N8 118.3(4) . . ? N10 C15 N9 117.3(4) . . ? N8 C15 N9 124.4(4) . . ? N10 C16 C17 112.7(5) . . ? N10 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? N10 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N10 C18 C19 112.1(5) . . ? N10 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? N10 C18 H18B 109.2 . . ? C19 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 N4 Co 172.7(4) . . ? C2 N5 Co 170.2(4) . . ? C3 N3 N7 105.5(3) . . ? C3 N3 Co 141.5(3) . . ? N7 N3 Co 113.0(2) . . ? C14 N1 C13 113.6(3) . . ? C14 N1 Co 123.2(3) . . ? C13 N1 Co 123.0(3) . . ? C8 N2 N6 105.7(3) . . ? C8 N2 Co 141.2(3) . . ? N6 N2 Co 113.0(2) . . ? C10 N6 N2 111.1(3) . . ? C10 N6 C13 131.9(3) . . ? N2 N6 C13 116.7(3) . . ? N3 N7 C5 111.7(3) . . ? N3 N7 C14 116.9(3) . . ? C5 N7 C14 131.5(4) . . ? C14 N8 C15 114.8(3) . . ? C13 N9 C15 113.6(3) . . ? C15 N10 C16 120.4(4) . . ? C15 N10 C18 120.3(4) . . ? C16 N10 C18 119.3(4) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.845 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 921715' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H26 N14 Ni O' _chemical_formula_weight 501.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.9708(7) _cell_length_b 15.4535(8) _cell_length_c 11.0815(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.1740(10) _cell_angle_gamma 90.00 _cell_volume 2297.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9943 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 28.50 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.886 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.742 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28290 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0125 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.50 _reflns_number_total 5557 _reflns_number_gt 4731 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+2.4493P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5557 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1464 _refine_ls_wR_factor_gt 0.1339 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.37785(2) 1.01237(2) -0.04979(3) 0.03981(13) Uani 1 1 d . . . C1 C 0.3406(2) 0.80480(19) -0.1131(3) 0.0458(6) Uani 1 1 d . . . C2 C 0.2824(2) 0.74013(18) -0.0776(3) 0.0497(6) Uani 1 1 d . . . H2A H 0.2779 0.6824 -0.1024 0.060 Uiso 1 1 calc R . . C3 C 0.2339(2) 0.77799(17) -0.0003(3) 0.0434(5) Uani 1 1 d . . . C4 C 0.4053(2) 0.7977(2) -0.1998(3) 0.0622(8) Uani 1 1 d . . . H4A H 0.4605 0.8369 -0.1732 0.093 Uiso 1 1 calc R . . H4B H 0.3671 0.8120 -0.2837 0.093 Uiso 1 1 calc R . . H4C H 0.4298 0.7395 -0.1983 0.093 Uiso 1 1 calc R . . C5 C 0.1621(2) 0.74024(19) 0.0628(3) 0.0552(7) Uani 1 1 d . . . H5A H 0.1621 0.6783 0.0554 0.083 Uiso 1 1 calc R . . H5B H 0.0964 0.7620 0.0235 0.083 Uiso 1 1 calc R . . H5C H 0.1815 0.7561 0.1500 0.083 Uiso 1 1 calc R . . C6 C 0.3685(2) 1.2279(2) -0.0374(3) 0.0501(6) Uani 1 1 d . . . C7 C 0.3098(2) 1.2868(2) 0.0074(3) 0.0586(8) Uani 1 1 d . . . H7A H 0.3086 1.3466 -0.0030 0.070 Uiso 1 1 calc R . . C8 C 0.2549(2) 1.24037(18) 0.0688(3) 0.0506(7) Uani 1 1 d . . . C9 C 0.4385(3) 1.2466(3) -0.1141(4) 0.0696(10) Uani 1 1 d . . . H9A H 0.4733 1.1946 -0.1235 0.104 Uiso 1 1 calc R . . H9B H 0.4856 1.2898 -0.0727 0.104 Uiso 1 1 calc R . . H9C H 0.4016 1.2673 -0.1954 0.104 Uiso 1 1 calc R . . C10 C 0.1800(3) 1.2699(2) 0.1322(4) 0.0688(10) Uani 1 1 d . . . H10A H 0.1766 1.3320 0.1302 0.103 Uiso 1 1 calc R . . H10B H 0.1991 1.2504 0.2178 0.103 Uiso 1 1 calc R . . H10C H 0.1159 1.2464 0.0894 0.103 Uiso 1 1 calc R . . C11 C 0.24229(18) 1.07847(16) 0.0918(3) 0.0403(5) Uani 1 1 d . . . C12 C 0.23365(18) 0.93440(16) 0.0672(2) 0.0388(5) Uani 1 1 d . . . C13 C 0.1447(2) 1.00041(18) 0.1789(3) 0.0498(7) Uani 1 1 d . . . C14 C 0.0549(3) 1.0752(3) 0.3103(4) 0.0769(11) Uani 1 1 d . . . H14A H 0.0405 1.0603 0.3885 0.092 Uiso 1 1 calc R . . H14B H 0.1100 1.1159 0.3290 0.092 Uiso 1 1 calc R . . C15 C -0.0323(4) 1.1148(4) 0.2248(5) 0.1043(16) Uani 1 1 d . . . H15A H -0.0503 1.1658 0.2629 0.156 Uiso 1 1 calc R . . H15B H -0.0868 1.0745 0.2070 0.156 Uiso 1 1 calc R . . H15C H -0.0175 1.1302 0.1481 0.156 Uiso 1 1 calc R . . C16 C 0.0419(3) 0.9108(2) 0.2764(3) 0.0646(9) Uani 1 1 d . . . H16A H 0.0935 0.8671 0.2889 0.078 Uiso 1 1 calc R . . H16B H 0.0211 0.9146 0.3528 0.078 Uiso 1 1 calc R . . C17 C -0.0440(3) 0.8847(3) 0.1711(4) 0.0844(12) Uani 1 1 d . . . H17A H -0.0689 0.8299 0.1898 0.127 Uiso 1 1 calc R . . H17B H -0.0233 0.8798 0.0957 0.127 Uiso 1 1 calc R . . H17C H -0.0956 0.9275 0.1593 0.127 Uiso 1 1 calc R . . N1 N 0.27567(16) 1.00816(13) 0.0474(2) 0.0414(5) Uani 1 1 d . . . N2 N 0.35290(16) 1.14793(15) -0.0056(2) 0.0453(5) Uani 1 1 d . . . N3 N 0.33082(16) 0.87929(15) -0.0598(2) 0.0425(5) Uani 1 1 d . . . N4 N 0.50157(17) 1.01025(16) -0.1159(2) 0.0455(5) Uani 1 1 d . . . N5 N 0.2784(2) 1.0393(2) -0.2207(3) 0.0747(8) Uani 1 1 d . . . N6 N 0.28238(16) 1.15512(14) 0.0606(2) 0.0434(5) Uani 1 1 d . . . N7 N 0.26464(15) 0.86312(13) 0.0103(2) 0.0401(5) Uani 1 1 d . . . N8 N 0.16756(18) 0.92506(15) 0.1297(2) 0.0490(5) Uani 1 1 d . . . N9 N 0.17705(19) 1.08037(15) 0.1561(2) 0.0511(6) Uani 1 1 d . . . N10 N 0.0828(2) 0.99568(18) 0.2514(3) 0.0605(7) Uani 1 1 d . . . N11 N 0.5052(3) 1.0270(3) -0.2175(3) 0.0900(12) Uani 1 1 d . . . N12 N 0.5089(5) 1.0442(7) -0.3159(5) 0.227(4) Uani 1 1 d . . . N13 N 0.2448(3) 1.00577(17) -0.3111(3) 0.0628(7) Uani 1 1 d . . . N14 N 0.2094(7) 0.9763(4) -0.4095(6) 0.178(3) Uani 1 1 d . . . O1W O 0.3147(4) -0.0150(3) 0.4023(6) 0.1539(19) Uani 1 1 d . . . H1WA H 0.3673 -0.0038 0.4686 0.231 Uiso 1 1 d R . . H1WB H 0.3152 0.0214 0.3391 0.231 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.03259(18) 0.0436(2) 0.0478(2) 0.00065(13) 0.01883(14) -0.00033(12) C1 0.0408(13) 0.0504(15) 0.0470(14) -0.0115(11) 0.0137(11) 0.0018(11) C2 0.0524(15) 0.0409(14) 0.0563(16) -0.0104(12) 0.0157(13) -0.0009(11) C3 0.0445(13) 0.0368(12) 0.0487(14) -0.0018(10) 0.0125(11) -0.0018(10) C4 0.0563(17) 0.073(2) 0.0649(19) -0.0247(16) 0.0303(15) -0.0024(15) C5 0.0637(18) 0.0421(14) 0.0655(18) 0.0016(13) 0.0277(15) -0.0099(13) C6 0.0416(13) 0.0479(15) 0.0601(17) 0.0079(12) 0.0131(12) -0.0068(11) C7 0.0604(18) 0.0384(14) 0.078(2) 0.0009(14) 0.0208(16) -0.0076(12) C8 0.0507(15) 0.0354(13) 0.0672(18) -0.0092(12) 0.0191(13) -0.0049(11) C9 0.0605(19) 0.070(2) 0.086(2) 0.0232(19) 0.0337(18) -0.0085(16) C10 0.074(2) 0.0416(16) 0.102(3) -0.0201(17) 0.043(2) -0.0026(14) C11 0.0378(12) 0.0363(12) 0.0510(14) -0.0013(10) 0.0196(10) -0.0012(9) C12 0.0369(11) 0.0349(11) 0.0489(13) -0.0010(10) 0.0194(10) -0.0005(9) C13 0.0499(15) 0.0482(15) 0.0608(17) -0.0028(12) 0.0310(14) 0.0010(11) C14 0.083(3) 0.079(3) 0.087(3) 0.001(2) 0.054(2) 0.008(2) C15 0.093(3) 0.098(4) 0.128(4) 0.003(3) 0.039(3) 0.013(3) C16 0.0648(19) 0.071(2) 0.070(2) 0.0102(17) 0.0392(17) 0.0064(16) C17 0.063(2) 0.098(3) 0.100(3) 0.004(2) 0.037(2) 0.002(2) N1 0.0362(10) 0.0367(10) 0.0591(13) -0.0035(9) 0.0259(10) -0.0012(8) N2 0.0388(10) 0.0434(12) 0.0590(13) 0.0030(10) 0.0224(10) -0.0018(9) N3 0.0384(11) 0.0453(12) 0.0496(12) -0.0068(9) 0.0217(9) -0.0002(9) N4 0.0393(11) 0.0597(14) 0.0432(11) 0.0021(10) 0.0208(9) -0.0004(9) N5 0.0709(19) 0.073(2) 0.071(2) 0.0074(16) 0.0039(16) 0.0130(16) N6 0.0409(11) 0.0367(11) 0.0580(13) -0.0034(9) 0.0224(10) -0.0031(8) N7 0.0393(10) 0.0364(10) 0.0499(12) -0.0039(9) 0.0212(9) -0.0022(8) N8 0.0520(13) 0.0417(12) 0.0652(14) -0.0037(10) 0.0360(12) -0.0053(10) N9 0.0565(13) 0.0415(12) 0.0679(15) -0.0057(11) 0.0382(12) 0.0000(10) N10 0.0621(16) 0.0600(16) 0.0746(18) 0.0002(13) 0.0444(15) 0.0024(12) N11 0.067(2) 0.154(4) 0.0596(18) 0.023(2) 0.0367(16) 0.016(2) N12 0.160(6) 0.456(13) 0.092(4) 0.095(6) 0.083(4) 0.071(7) N13 0.086(2) 0.0442(14) 0.0556(16) 0.0032(12) 0.0148(15) -0.0060(13) N14 0.285(9) 0.094(4) 0.107(4) -0.020(3) -0.022(5) -0.049(4) O1W 0.134(4) 0.150(4) 0.169(5) -0.006(3) 0.028(4) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni N1 2.014(2) . ? Ni N5 2.055(3) . ? Ni N4 2.057(2) . ? Ni N4 2.147(2) 3_675 ? Ni N3 2.152(2) . ? Ni N2 2.201(2) . ? C1 N3 1.318(3) . ? C1 C2 1.412(4) . ? C1 C4 1.495(4) . ? C2 C3 1.362(4) . ? C2 H2A 0.9300 . ? C3 N7 1.379(3) . ? C3 C5 1.493(4) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N2 1.320(4) . ? C6 C7 1.405(4) . ? C6 C9 1.491(4) . ? C7 C8 1.363(4) . ? C7 H7A 0.9300 . ? C8 N6 1.382(3) . ? C8 C10 1.485(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N9 1.304(3) . ? C11 N1 1.330(3) . ? C11 N6 1.394(3) . ? C12 N8 1.307(3) . ? C12 N1 1.328(3) . ? C12 N7 1.396(3) . ? C13 N10 1.337(4) . ? C13 N8 1.361(4) . ? C13 N9 1.363(4) . ? C14 C15 1.454(6) . ? C14 N10 1.494(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.477(6) . ? C16 N10 1.488(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? N2 N6 1.387(3) . ? N3 N7 1.386(3) . ? N4 N11 1.169(4) . ? N4 Ni 2.147(2) 3_675 ? N5 N13 1.110(4) . ? N11 N12 1.138(5) . ? N13 N14 1.157(6) . ? O1W H1WA 0.9000 . ? O1W H1WB 0.8999 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni N5 95.80(12) . . ? N1 Ni N4 168.76(10) . . ? N5 Ni N4 95.43(12) . . ? N1 Ni N4 92.39(9) . 3_675 ? N5 Ni N4 171.56(12) . 3_675 ? N4 Ni N4 76.41(10) . 3_675 ? N1 Ni N3 75.23(8) . . ? N5 Ni N3 91.58(12) . . ? N4 Ni N3 103.95(9) . . ? N4 Ni N3 92.52(9) 3_675 . ? N1 Ni N2 74.45(8) . . ? N5 Ni N2 84.50(12) . . ? N4 Ni N2 107.18(9) . . ? N4 Ni N2 95.72(9) 3_675 . ? N3 Ni N2 148.85(8) . . ? N3 C1 C2 110.7(2) . . ? N3 C1 C4 120.6(3) . . ? C2 C1 C4 128.7(3) . . ? C3 C2 C1 107.3(2) . . ? C3 C2 H2A 126.4 . . ? C1 C2 H2A 126.4 . . ? C2 C3 N7 105.5(2) . . ? C2 C3 C5 130.0(3) . . ? N7 C3 C5 124.5(2) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C7 110.8(3) . . ? N2 C6 C9 121.1(3) . . ? C7 C6 C9 128.0(3) . . ? C8 C7 C6 107.5(3) . . ? C8 C7 H7A 126.2 . . ? C6 C7 H7A 126.2 . . ? C7 C8 N6 105.3(3) . . ? C7 C8 C10 130.0(3) . . ? N6 C8 C10 124.7(3) . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N9 C11 N1 126.3(2) . . ? N9 C11 N6 120.4(2) . . ? N1 C11 N6 113.3(2) . . ? N8 C12 N1 126.3(2) . . ? N8 C12 N7 120.4(2) . . ? N1 C12 N7 113.3(2) . . ? N10 C13 N8 117.2(3) . . ? N10 C13 N9 117.7(2) . . ? N8 C13 N9 125.0(2) . . ? C15 C14 N10 109.6(4) . . ? C15 C14 H14A 109.8 . . ? N10 C14 H14A 109.8 . . ? C15 C14 H14B 109.8 . . ? N10 C14 H14B 109.8 . . ? H14A C14 H14B 108.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 N10 111.3(3) . . ? C17 C16 H16A 109.4 . . ? N10 C16 H16A 109.4 . . ? C17 C16 H16B 109.4 . . ? N10 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C12 N1 C11 115.0(2) . . ? C12 N1 Ni 121.86(17) . . ? C11 N1 Ni 123.06(17) . . ? C6 N2 N6 105.1(2) . . ? C6 N2 Ni 141.6(2) . . ? N6 N2 Ni 111.95(15) . . ? C1 N3 N7 105.2(2) . . ? C1 N3 Ni 142.12(19) . . ? N7 N3 Ni 112.64(15) . . ? N11 N4 Ni 127.3(2) . . ? N11 N4 Ni 128.7(2) . 3_675 ? Ni N4 Ni 103.59(10) . 3_675 ? N13 N5 Ni 138.2(3) . . ? C8 N6 N2 111.2(2) . . ? C8 N6 C11 130.9(2) . . ? N2 N6 C11 117.2(2) . . ? C3 N7 N3 111.4(2) . . ? C3 N7 C12 131.6(2) . . ? N3 N7 C12 116.7(2) . . ? C12 N8 C13 113.4(2) . . ? C11 N9 C13 113.5(2) . . ? C13 N10 C16 120.4(3) . . ? C13 N10 C14 120.6(3) . . ? C16 N10 C14 119.0(3) . . ? N12 N11 N4 179.3(8) . . ? N5 N13 N14 175.3(5) . . ? H1WA O1W H1WB 109.5 . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 1.073 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 921716' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_wx60 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H24 Co N14' _chemical_formula_weight 483.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.860(4) _cell_length_b 11.386(4) _cell_length_c 11.379(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.365(7) _cell_angle_gamma 90.00 _cell_volume 2174.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1772 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 28.67 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1004 _exptl_absorpt_coefficient_mu 0.827 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.653 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6532 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1912 _reflns_number_gt 1468 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1912 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co Co 1.0000 0.75668(4) 0.2500 0.0410(2) Uani 1 2 d S . . C1 C 0.95878(15) 0.5145(2) 0.1666(2) 0.0361(6) Uani 1 1 d . . . C2 C 1.0000 0.3446(3) 0.2500 0.0379(9) Uani 1 2 d S . . C3 C 0.95817(16) 0.1638(2) 0.1516(2) 0.0453(7) Uani 1 1 d . . . H3A H 0.9804 0.0853 0.1498 0.054 Uiso 1 1 calc R . . H3B H 0.9674 0.2022 0.0780 0.054 Uiso 1 1 calc R . . C4 C 0.86983(18) 0.1546(3) 0.1598(3) 0.0564(8) Uani 1 1 d . . . H4A H 0.8458 0.1111 0.0935 0.085 Uiso 1 1 calc R . . H4B H 0.8471 0.2320 0.1597 0.085 Uiso 1 1 calc R . . H4C H 0.8602 0.1150 0.2315 0.085 Uiso 1 1 calc R . . C5 C 0.86579(15) 0.5544(2) -0.0169(2) 0.0385(6) Uani 1 1 d . . . C6 C 0.84011(16) 0.6580(2) -0.0642(2) 0.0433(7) Uani 1 1 d . . . H6A H 0.8064 0.6681 -0.1329 0.052 Uiso 1 1 calc R . . C7 C 0.87366(16) 0.7478(2) 0.0093(2) 0.0392(6) Uani 1 1 d . . . C8 C 0.86285(19) 0.8775(3) 0.0001(3) 0.0532(8) Uani 1 1 d . . . H8A H 0.8540 0.9089 0.0761 0.080 Uiso 1 1 calc R . . H8B H 0.8178 0.8949 -0.0551 0.080 Uiso 1 1 calc R . . H8C H 0.9098 0.9124 -0.0266 0.080 Uiso 1 1 calc R . . C9 C 0.84606(17) 0.4320(3) -0.0551(3) 0.0517(7) Uani 1 1 d . . . H9A H 0.8165 0.4332 -0.1314 0.078 Uiso 1 1 calc R . . H9B H 0.8145 0.3956 0.0008 0.078 Uiso 1 1 calc R . . H9C H 0.8944 0.3882 -0.0593 0.078 Uiso 1 1 calc R . . N1 N 1.0000 0.5790(3) 0.2500 0.0385(7) Uani 1 2 d S . . N2 N 0.91918(13) 0.70353(19) 0.09778(19) 0.0419(5) Uani 1 1 d . . . N3 N 1.07165(16) 0.8510(2) 0.1617(2) 0.0561(7) Uani 1 1 d . . . N4 N 0.95656(12) 0.40073(18) 0.15904(18) 0.0374(5) Uani 1 1 d . . . N5 N 1.0000 0.2293(2) 0.2500 0.0391(7) Uani 1 2 d S . . N6 N 0.91493(12) 0.58292(18) 0.08288(18) 0.0374(5) Uani 1 1 d . . . N7 N 1.14174(17) 0.8635(2) 0.1778(2) 0.0486(6) Uani 1 1 d . . . N8 N 1.20910(18) 0.8803(3) 0.1883(3) 0.0776(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.0551(4) 0.0279(3) 0.0394(3) 0.000 0.0002(2) 0.000 C1 0.0392(14) 0.0352(15) 0.0333(14) -0.0004(11) 0.0006(11) -0.0002(11) C2 0.040(2) 0.032(2) 0.042(2) 0.000 0.0056(17) 0.000 C3 0.0598(18) 0.0311(14) 0.0440(16) -0.0076(12) -0.0002(14) 0.0004(12) C4 0.062(2) 0.0435(17) 0.062(2) -0.0091(14) -0.0006(16) -0.0096(14) C5 0.0405(14) 0.0423(15) 0.0321(14) -0.0024(11) 0.0007(11) -0.0045(12) C6 0.0439(15) 0.0494(17) 0.0351(14) 0.0066(12) -0.0036(12) -0.0001(13) C7 0.0413(15) 0.0398(15) 0.0364(14) 0.0048(12) 0.0022(11) 0.0016(12) C8 0.0665(19) 0.0423(17) 0.0507(17) 0.0104(14) 0.0052(15) 0.0086(14) C9 0.0597(18) 0.0490(18) 0.0444(16) -0.0032(14) -0.0060(14) -0.0063(14) N1 0.0461(17) 0.0299(16) 0.0369(17) 0.000 -0.0100(14) 0.000 N2 0.0558(14) 0.0297(11) 0.0387(12) 0.0050(10) -0.0027(11) 0.0028(11) N3 0.0597(17) 0.0568(17) 0.0504(15) 0.0129(12) -0.0030(13) -0.0073(13) N4 0.0445(12) 0.0290(12) 0.0367(12) 0.0003(9) -0.0057(10) 0.0007(9) N5 0.0483(19) 0.0248(17) 0.0429(18) 0.000 -0.0030(14) 0.000 N6 0.0473(12) 0.0304(11) 0.0326(11) 0.0014(9) -0.0062(10) -0.0008(10) N7 0.0655(19) 0.0424(14) 0.0368(13) 0.0022(10) -0.0009(12) 0.0029(12) N8 0.0589(18) 0.095(2) 0.077(2) 0.0082(18) -0.0009(16) -0.0014(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co N3 1.962(3) 2_755 ? Co N3 1.962(3) . ? Co N1 2.023(3) . ? Co N2 2.187(2) 2_755 ? Co N2 2.187(2) . ? C1 N4 1.298(3) . ? C1 N1 1.341(3) . ? C1 N6 1.389(3) . ? C2 N5 1.313(4) . ? C2 N4 1.369(3) 2_755 ? C2 N4 1.369(3) . ? C3 N5 1.470(3) . ? C3 C4 1.505(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.351(4) . ? C5 N6 1.381(3) . ? C5 C9 1.488(4) . ? C6 C7 1.405(4) . ? C6 H6A 0.9300 . ? C7 N2 1.308(3) . ? C7 C8 1.491(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? N1 C1 1.341(3) 2_755 ? N2 N6 1.385(3) . ? N3 N7 1.187(3) . ? N5 C3 1.470(3) 2_755 ? N7 N8 1.147(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Co N3 113.61(16) 2_755 . ? N3 Co N1 123.20(8) 2_755 . ? N3 Co N1 123.19(8) . . ? N3 Co N2 96.53(10) 2_755 2_755 ? N3 Co N2 100.91(10) . 2_755 ? N1 Co N2 73.93(6) . 2_755 ? N3 Co N2 100.91(10) 2_755 . ? N3 Co N2 96.53(10) . . ? N1 Co N2 73.93(6) . . ? N2 Co N2 147.87(12) 2_755 . ? N4 C1 N1 127.1(2) . . ? N4 C1 N6 120.3(2) . . ? N1 C1 N6 112.6(2) . . ? N5 C2 N4 117.82(16) . 2_755 ? N5 C2 N4 117.82(16) . . ? N4 C2 N4 124.4(3) 2_755 . ? N5 C3 C4 113.3(2) . . ? N5 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N5 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 N6 105.5(2) . . ? C6 C5 C9 130.3(2) . . ? N6 C5 C9 124.1(2) . . ? C5 C6 C7 107.6(2) . . ? C5 C6 H6A 126.2 . . ? C7 C6 H6A 126.2 . . ? N2 C7 C6 110.6(2) . . ? N2 C7 C8 119.6(2) . . ? C6 C7 C8 129.7(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 N1 C1 113.6(3) . 2_755 ? C1 N1 Co 123.21(15) . . ? C1 N1 Co 123.21(15) 2_755 . ? C7 N2 N6 105.5(2) . . ? C7 N2 Co 141.28(19) . . ? N6 N2 Co 113.12(15) . . ? N7 N3 Co 129.7(2) . . ? C1 N4 C2 113.9(2) . . ? C2 N5 C3 120.50(14) . 2_755 ? C2 N5 C3 120.50(14) . . ? C3 N5 C3 119.0(3) 2_755 . ? C5 N6 N2 110.7(2) . . ? C5 N6 C1 132.2(2) . . ? N2 N6 C1 117.0(2) . . ? N8 N7 N3 176.1(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.431 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 921717'